What are some ways in which expensive products can be worse than cheaper ones?

Examples that come to my mind:

* Expensive clothes can be much less convenient to clean
* In expensive hotel rooms it's often harder to figure out how to turn off all the lights
* Expensive restaurants often have less choice in menus

* but expensive clothes can (not always) feel better because of better fabrics
* but are cleaner, smell better, offer more services, better food
* but may be the result of an expert making the choice for you.

Changing specs may result in increased cost but may come with other improvements.

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For me the most pleasant fabric is the Uniqlo airism T shirts, which are $15 each!

Fair. But I think there is a point in using more in one dimensions when evaluating something. A single good-bad scale is not enough. For example the flex-scale :-) 

But I guess you already asked about "ways" which is the same.

Agree! And I do think the answers to a lot of these are going to be very personal. As I explained in my other answer, I uniquely despise small-menu restaurants and especially omakase because I have picky food preferences, but if you are not that then that argument does not apply and you may enjoy them!